TWI290554B - Process for preparation 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination - Google Patents

Process for preparation 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination Download PDF

Info

Publication number
TWI290554B
TWI290554B TW089125682A TW89125682A TWI290554B TW I290554 B TWI290554 B TW I290554B TW 089125682 A TW089125682 A TW 089125682A TW 89125682 A TW89125682 A TW 89125682A TW I290554 B TWI290554 B TW I290554B
Authority
TW
Taiwan
Prior art keywords
butyl
tert
group
formula
compound
Prior art date
Application number
TW089125682A
Other languages
English (en)
Chinese (zh)
Inventor
Andreas Bathe
Steffen Emmert
Bernd Helfert
Henning Boettcher
Original Assignee
Merck Patent Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Application granted granted Critical
Publication of TWI290554B publication Critical patent/TWI290554B/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
TW089125682A 1999-12-04 2000-12-02 Process for preparation 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination TWI290554B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19958496A DE19958496A1 (de) 1999-12-04 1999-12-04 Verfahren zur Herstellung von 5-(1-Piperazinyl)-benzofuran-2-carboxamid durch Übergangsmetallkatalysierte Aminierung

Publications (1)

Publication Number Publication Date
TWI290554B true TWI290554B (en) 2007-12-01

Family

ID=7931421

Family Applications (1)

Application Number Title Priority Date Filing Date
TW089125682A TWI290554B (en) 1999-12-04 2000-12-02 Process for preparation 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination

Country Status (29)

Country Link
US (1) US6762300B2 (da)
EP (1) EP1233961B9 (da)
JP (1) JP4897174B2 (da)
KR (1) KR100759072B1 (da)
CN (1) CN1232519C (da)
AR (1) AR026677A1 (da)
AT (1) ATE299141T1 (da)
AU (1) AU783355B2 (da)
BR (1) BR0016149B1 (da)
CA (1) CA2393183C (da)
CZ (1) CZ300428B6 (da)
DE (2) DE19958496A1 (da)
DK (1) DK1233961T3 (da)
ES (1) ES2243347T3 (da)
HK (1) HK1053471A1 (da)
HU (1) HU228841B1 (da)
IL (2) IL149974A0 (da)
MX (1) MXPA02005515A (da)
MY (1) MY127851A (da)
NO (1) NO327913B1 (da)
PL (1) PL199197B1 (da)
PT (1) PT1233961E (da)
RU (1) RU2266292C2 (da)
SI (1) SI1233961T1 (da)
SK (1) SK287467B6 (da)
TW (1) TWI290554B (da)
UA (1) UA76944C2 (da)
WO (1) WO2001040219A2 (da)
ZA (1) ZA200205326B (da)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006060597A1 (de) * 2006-12-21 2008-06-26 Merck Patent Gmbh Verfahren zur Herstellung von Benzofuran-2-carboxamiden
EP2110374A1 (en) * 2008-04-18 2009-10-21 Merck Sante Benzofurane, benzothiophene, benzothiazol derivatives as FXR modulators
UY32481A (es) * 2009-03-10 2010-09-30 Takeda Pharmaceutical Derivados de benzofurano
CZ305317B6 (cs) * 2011-12-20 2015-07-29 Masarykova Univerzita Způsob přímé mono-N-substituce piperazinu
WO2013168126A1 (en) 2012-05-11 2013-11-14 Dr.Reddys Laboratories Limited Crystalline forms of vilazodone hydrochloride and vilazodone free base
CN102964323B (zh) * 2012-11-13 2015-03-25 苏州永健生物医药有限公司 一种5-（哌嗪-1-基）苯并呋喃-2-甲酰胺的合成方法
CN104045608B (zh) * 2013-03-11 2016-06-01 天津药物研究院有限公司 一种取代哌嗪化合物及制备维拉佐酮中间体的方法
CN103360374B (zh) * 2013-07-12 2016-03-09 苏州永健生物医药有限公司 维拉唑酮及其盐的合成方法
CN103965148B (zh) * 2014-05-15 2016-04-06 北京北陆药业股份有限公司 一种5-(哌嗪-1-基)苯并呋喃-2-羧酸乙酯的合成方法
CN105367525A (zh) * 2014-08-28 2016-03-02 天津药物研究院 一种取代苯并呋喃-2-甲酰胺的制备方法
CN113214200B (zh) * 2021-05-26 2022-03-29 神隆医药（常熟）有限公司 一种以铜催化偶联反应制备维拉佐酮中间体的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4210646A (en) * 1978-04-11 1980-07-01 Janssen Pharmaceutica N.V. Antimicrobial compositions containing 1-(aryloxyphenyl)piperazines
EP0264730B1 (en) * 1986-10-10 1993-07-14 Konica Corporation Silver halide photographic light-sensitive material to provide dye-image with improved color-fastness to light
DE19514567A1 (de) * 1995-04-20 1996-10-24 Merck Patent Gmbh Benzofurane
JP3161360B2 (ja) * 1996-04-19 2001-04-25 東ソー株式会社 アリールアミン類の製造方法
US5929281A (en) * 1996-04-19 1999-07-27 Tosoh Corporation Process for producing heterocyclic aromatic amine or arylamine
DE19650213A1 (de) * 1996-12-04 1998-06-10 Hoechst Ag Synthese von aromatischen Aminen aus Chloraromaten

Also Published As

Publication number Publication date
ES2243347T3 (es) 2005-12-01
DE19958496A1 (de) 2001-06-07
CN1232519C (zh) 2005-12-21
AU2838201A (en) 2001-06-12
CA2393183A1 (en) 2001-06-07
JP2003515605A (ja) 2003-05-07
KR20020062313A (ko) 2002-07-25
SK287467B6 (sk) 2010-10-07
SK7452002A3 (en) 2003-01-09
IL149974A0 (en) 2002-12-01
NO20022620L (no) 2002-07-30
KR100759072B1 (ko) 2007-09-19
US6762300B2 (en) 2004-07-13
CZ20021822A3 (cs) 2002-10-16
AU783355B2 (en) 2005-10-20
CN1407981A (zh) 2003-04-02
WO2001040219A2 (de) 2001-06-07
BR0016149A (pt) 2002-08-13
EP1233961A2 (de) 2002-08-28
BR0016149B1 (pt) 2011-02-22
MXPA02005515A (es) 2002-09-30
UA76944C2 (en) 2006-10-16
MY127851A (en) 2006-12-29
ATE299141T1 (de) 2005-07-15
HUP0203800A3 (en) 2004-12-28
DE50010680D1 (de) 2005-08-11
ZA200205326B (en) 2003-10-03
JP4897174B2 (ja) 2012-03-14
WO2001040219A3 (de) 2002-05-16
CA2393183C (en) 2009-12-29
EP1233961B1 (de) 2005-07-06
CZ300428B6 (cs) 2009-05-20
NO327913B1 (no) 2009-10-19
PL355227A1 (en) 2004-04-05
EP1233961B9 (de) 2012-03-21
DK1233961T3 (da) 2005-10-17
HU228841B1 (hu) 2013-06-28
NO20022620D0 (no) 2002-06-03
HUP0203800A2 (hu) 2003-04-28
SI1233961T1 (sl) 2005-12-31
PL199197B1 (pl) 2008-08-29
IL149974A (en) 2008-12-29
RU2266292C2 (ru) 2005-12-20
PT1233961E (pt) 2005-11-30
HK1053471A1 (en) 2003-10-24
AR026677A1 (es) 2003-02-19
US20030125558A1 (en) 2003-07-03

Similar Documents

Publication Publication Date Title
TW200403224A (en) Novel compounds
TWI290554B (en) Process for preparation 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination
EP0187524B1 (en) A diaryl butyric acid derivative and the production process thereof
IE77776B1 (en) New 5-isoquinolinesulfonamides process for preparing them and pharmaceutical compositions containing them
CN114349714B (zh) 一种二苯并二氮卓衍生物及其制备方法和应用
FR2674849A1 (fr) Nouveaux derives de n-cyclohexyl benzamides ou thiobenzamides, leurs preparations et leurs applications en therapeutique.
WO1998031677A1 (fr) Nouvelles amines aromatiques derivees d'amines cycliques utiles comme medicaments
EP0553016B1 (fr) Nouveaux amides et sulfonamides naphtaleniques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
JPS61238784A (ja) コハク酸イミド誘導体及びその酸付加塩
WO2000058301A1 (fr) Derives de n-[2-(4-aminophenyl)ethyl]-2,3-dihydro-1,4-benzodioxine-2-methanamine, leur preparation et leur application en therapeutique
FR2643634A1 (fr) Nouveaux derives benzoxazolinoniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
JPS6047255B2 (ja) ２−アミノ−５−スルフアモイル−安息香酸アミドの製法
FR2663929A1 (fr) Nouveaux derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
US3905990A (en) Basically substituted benzimidazole derivatives
JPH09505079A (ja) Ｎ−置換されたグリシンまたはグリシンエステルの製造方法ならびにインジゴ合成方法への適用
EP0402232A1 (fr) Dérivés de pyridobenzoindole, leur préparation et les compositions qui les contiennent
JP3245578B2 (ja) ピロリジニルヒドロキサム酸化合物の製造方法
CH633552A5 (fr) Procede de preparation de nouveaux benzothiophenes.
WO2006129781A1 (ja) ジベンズオキセピン誘導体の製造方法
EP0489548B1 (en) A process for the preparation of 2(R)-methyl-4,4,4-trifluorobutylamine, intermediates, and a process for the preparation of a derivative thereof
JPH0737442B2 (ja) アニリン類及びベンジルアミン類から得られるベンジルセレノベンズアミド類、及びその製造方法
JPH02207025A (ja) 有機合成法
JP2001270863A (ja) ６−置換インドール誘導体の製造方法
JPS635087A (ja) （＋）−トランス−１ａ，２，３，４ａ，５，６−ヘキサヒドロ−９−ヒドロキシ−４−プロピル−４Ｈ−ナフト〔１，２−ｂ〕−１，４−オキサジンのキラル合成
CA1050021A (en) 6-aza-3h-1,4-benzodiazepines

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees